29. They Acted Childish

While Darin emotionally manipulated Dee and often reduced her to tears, Dee eased her pain with a bottle every night. Wanting to retaliate, she would often find silly ways to criticize Darin’s looks.

Dee would demoralize Darin and tell him his toupee was crooked before he appeared on shows to “stir things up”. Darin, once he was done making Dee cry, tapped into his paranoid side and made everything even worse.

Universal Pictures ,That Funny Feeling (1965)

30. He Had Conspiracy Theories About His Wife

Darin often obsessed over Dee’s relationships with her coworkers. Since they had fallen in love on set, what was to stop her from having an affair with another one of her co-stars? Therefore, when Dee began the production of her new movie Tammy and the Doctor, Darin began acting overly suspicious every time Dee spent some time with her co-star Peter Fonda.

Universal Pictures,Wikimedia Commons

31. He Wanted Out

In 1963, Darin could no longer shake off the feeling that his wife was having an affair. He acted up and told her he wanted a divorce, telling Dee the nonsensical reason behind this decision. Dee was both furious and disappointed. She repeatedly denied the claims, eventually convincing Darin to rethink his accusations.

Sadly, this didn’t magically solve their problems.

Stanley Kramer Productions, Pressure Point (1962)

32. He Was Still Jealous

After almost breaking up with his wife, Darin felt like he needed to make an effort, and so did Dee. He committed all his time to being a good father and an easy-going husband, but there was one big issue: his jealousy. He was unreasonable and paranoid.

On one occasion, he lost his mind over the fact that Dee talked to Warren Beatty at a party. He was silent about it—but behind closed doors, it was a different story.

Globe. Photographer not credited, Wikimedia Commons

33. He Made A Decision

Darin didn’t know what to do or how to fix his jealousy problem, so he took the easy way out. Still, he wasn’t bold enough to face Dee, so he went behind her back. In a jaw-dropping act, he had his psychiatrist tell Dee that he wanted out. In the blink of an eye, they separated for good...and then began the hardest year of his life: 1968.

Stanley Kramer Productions, Pressure Point (1962)

34. He Made A New Friend

1968 started off as a very busy year for Darin—he became more politically active and worked on Robert F Kennedy’s presidential campaign. Beyond the working relationship, Kennedy and Darin developed a very close friendship. Darin considered Kennedy his hero, and one of the main reasons he got more involved in politics.

Soon after, Kennedy became the main reason for his grief.

Warren K. Leffler, U.S. News & World Report Magazine, Wikimedia Commons

35. He Suffered A Loss

Darin felt strongly about Kennedy—but he almost witnessed his demise. He was traveling with Kennedy and he even made it to the politician's final destination—California. Darin stayed at the Ambassador Hotel and was one of the last people who ever saw him before a horrendous assassination ripped Kennedy out of his life.

Yoichi Okamoto, Wikimedia Commons

36. He Didn't Leave His Side

Darin threw himself into recording new types of music while trying to shake off the trauma of losing Bobby Kennedy. He was so shaken by Kennedy’s death that, reportedly, when the coffin was above ground, awaiting burial, Darin stayed with Kennedy’s body all night.

But this wasn't the only event that turned Darin's life upside down.

Paramount Pictures, Too Late Blues (1961)

37. His Heart Couldn't Take It

Even though he worked tirelessly to live with it, Darin’s heart was very fragile—and he'd had a frail constitution since childhood. As time passed, his heart got weaker and weaker—but his divorce was the last nail in the coffin. By the 1970s, Darin's health was not doing well. He felt alone and miserable, so he went crawling back to Dee.

Stanley Kramer Productions, Pressure Point (1962)

38. His Ex-Wife Still Loved Him

In the 1970s, his ex-wife saw him getting sicker by the day—and despite their turbulent past, she couldn’t leave him alone like that. According to Dee, “He would come to the door with his vitamins and say, 'I have nowhere to go'". She knew she had a soft spot for Darin, so every time she would let him in and as she put it, “things would start again”.

However, it wasn't long before Darin began knocking on someone else’s door.

Universal Pictures ,That Funny Feeling (1965)

39. There Was Another Woman

In 1970, Darin found love for the second time—this time, she went by the name of Andrea Yeager. Unlike Dee, she wasn’t a world-class actress, but a humble secretary. Even Darin’s friends said that “You couldn't have a more stand-up person around you. She didn’t want anything from Bobby,” and Darin fell head over heels in love with her.

7 Pictures , Come September (1961)

40. He Underwent Surgery

After a year filled with medicine and dire side effects, Darin's doctors finally told him that his heart needed surgery. In January 1971, he underwent an artificial valve implant—a painful surgery with a long recovery period. When he opened his eyes, he began the next chapter of his life: trying to heal his broken heart.

CBS Television, Wikimedia Commons

41. Love Healed Him

According to one of Darin’s friends, Yeager was “willing to confront the grim reality of his illness and help him in any way she could” and it was working. Darin began performing again, and Yeager was there whenever he felt bad. Reportedly, Darin was often administered oxygen during or after he performed, but he kept performing, and Yeager kept helping him.

Yeager's devotion was undeniable and it influenced Darin to give love another shot.

ABC Television, Wikimedia Commons

42. She Became His Wife

After three years of living together, Darin and Yeager decided to turn it up a notch. In the summer of 1973, the two made their wedding vows and became husband and wife—they were already committed to each other in sickness and in health. However, Darin’s sickness tested their limits.

If Darin thought he'd found his "happily ever after," he was so wrong.

7 Pictures , Come September (1961)

43. They Fell Apart

Only four months later, Darin’s worsening health worsened his relationship. He was living in desperation and the woman he once loved had reached the end of her rope. In October 1973, the fairytale romance came to an end and they divorced.

Only 37 years old, Darin was a divorced man for the second time—but fate had another horrible twist in store for him.

Stanley Kramer Productions, Pressure Point (1962)

44. His Last Visit Was Unexpected

The same year, Darin made a mistake that led to serious consequences. When he had a dental appointment in 1973, he failed to take his antibiotics—which protected his heart. This caused an overwhelming systemic infection and weakened his heart to very dangerous levels. Due to sepsis, he ended up in the hospital.

Sadly, this was the beginning of the end.

Stanley Kramer Productions, Pressure Point (1962)

45. He Never Woke Up

On December 11, 1973, Darin scheduled another hazardous heart surgery at the Cedars of Lebanon Hospital in Los Angeles. A surgical team worked for six hours straight to repair his heart for the second time. Sadly, this second operation time wasn’t as successful as the one he'd had in 1971. Bobby Darin never woke up. Only 37 years old, the musician passed away in the recovery room.

Pax Enterprises , The Happy Ending (1969)

46. They Made A Movie About Him

Darin’s early death shook some people, while his action-filled life inspired others to share his story. Director Barry Levinson was in the latter group. In 1997, he began working on a film that intended to tell Darin's crazy life story—but like most of Darin’s dreams, it remained unfinished. However, someone else had their eye on the singer's legacy.

Kevin Spacey took over the project along with the help of Darin’s son, Dodd. The result? A biopic called Beyond the Sea.

Lions Gate Films , Beyond the Sea (2004)

47. His Legacy Was Gone

It seemed like tragedy followed Darin wherever he went, even after his death. In 2008, The New York Times reported that in the Universal Studios fire, Darin’s work—among hundreds of other artists—was destroyed. Based on what we know of him, it was probably best that Darin was not alive to witness this tragedy.

pinguino k, CC BY 2.0 , Wikimedia Commons

48. They Made A Musical Too

Dodd Darin got involved in a musical project to commemorate his father. The musical—called Dream Lover: The Bobby Darin Musical—aimed to delve deeper into Darin’s problematic relationship with his mother and grandmother. However, Dodd had something heartbreaking to say about the casting of David Campbell in the lead role.

Universal Pictures ,That Funny Feeling (1965)

49. His Son Knew He Was The Right Fit

Dodd noted that “You have to have lived something like that to understand it and [Campbell] has, and I think he can relate to my dad, he can relate to the pain”. Campbell must have been a perfect fit to play Darin because the musical received very positive reviews.

After it premiered in 2016, the production got best musical and best male lead nominations. More importantly, it gave Darin and his human side the recognition he deserved.

7 Pictures , Come September (1961)

50. He Learned His Family's Secret

The same year Darin lost Kennedy, he learned something jaw-dropping about his own past. He discovered his family's wildest secret. See, his mother Nina was just 17 years old when she had him, and to cover up her teen pregnancy she passed him off as her younger brother. Instead, Darin grew up believing his grandmother was his mother.

Nina finally confessed this, sending Darin into a tailspin.  However, there was another question on the tip of his tongue.

Universal International Pictures, If a Man Answers (1962)

51. He Wanted To Learn Everything

This revelation devastated Darin. There were so many unanswered questions, namely, who was his father? Unfortunately, he never got a satisfactory answer. His real mother refused to reveal the identity of Darin’s father.

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Universal Pictures ,That Funny Feeling (1965)